JPH01104085A - ホスホン酸誘導体およびそのエナンチオ選択的製造 - Google Patents

ホスホン酸誘導体およびそのエナンチオ選択的製造

Info

Publication number: JPH01104085A
Authority: JP; Japan
Prior art keywords: group; formula; general formula; acid; lower alkyl
Prior art date: 1987-07-15
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP63177950A

Other languages

English (en)

Japanese (ja)

Inventor

Graziano Castaldi

カスタルディグラツィアーノ

Claudio Giordano

クラウディオ　ジオルダーノ

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Zambon Group SpA

Zambon SpA

Original Assignee

Zambon Group SpA

Zambon SpA

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1987-07-15

Filing date

1988-07-15

Publication date

1989-04-21

1987-07-15 Priority claimed from IT21303/87A external-priority patent/IT1222041B/it

1987-12-21 Priority claimed from IT23125/87A external-priority patent/IT1223564B/it

1988-07-15 Application filed by Zambon Group SpA, Zambon SpA filed Critical Zambon Group SpA

1989-04-21 Publication of JPH01104085A publication Critical patent/JPH01104085A/ja

Status Pending legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 20
150000003007 phosphonic acid derivatives Chemical class 0.000 title 1
-1 sulfonic acid halide Chemical class 0.000 claims abstract description 32
239000002253 acid Substances 0.000 claims abstract description 21
125000000217 alkyl group Chemical group 0.000 claims abstract description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 9
239000012442 inert solvent Substances 0.000 claims abstract description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
229910052708 sodium Inorganic materials 0.000 claims abstract description 5
SYUQQUMHOZQROL-UHFFFAOYSA-N trimethylsilyl dihydrogen phosphite Chemical compound C[Si](C)(C)OP(O)O SYUQQUMHOZQROL-UHFFFAOYSA-N 0.000 claims abstract description 5
MXMXXUIOCREOTJ-HRFVKAFMSA-N (1S,2S)-1,2-dihydroxypropylphosphonic acid Chemical compound C[C@H](O)[C@@H](O)P(O)(O)=O MXMXXUIOCREOTJ-HRFVKAFMSA-N 0.000 claims abstract description 4
229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
FMNMEQSRDWIBFO-UHFFFAOYSA-N propanoyl phosphate Chemical compound CCC(=O)OP(O)(O)=O FMNMEQSRDWIBFO-UHFFFAOYSA-N 0.000 claims abstract 2
150000001875 compounds Chemical class 0.000 claims description 66
238000006243 chemical reaction Methods 0.000 claims description 44
239000002904 solvent Substances 0.000 claims description 30
125000004432 carbon atom Chemical group C* 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 10
239000000126 substance Substances 0.000 claims description 9
125000002877 alkyl aryl group Chemical group 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 4
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 3
MIOPJNTWMNEORI-XVKPBYJWSA-N (R)-camphorsulfonic acid Chemical compound C1C[C@]2(CS(O)(=O)=O)C(=O)C[C@H]1C2(C)C MIOPJNTWMNEORI-XVKPBYJWSA-N 0.000 claims description 2
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
239000003054 catalyst Substances 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 2
125000005207 tetraalkylammonium group Chemical group 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 3
239000011734 sodium Substances 0.000 claims 3
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 claims 1
FRYHCSODNHYDPU-UHFFFAOYSA-N ethanesulfonyl chloride Chemical compound CCS(Cl)(=O)=O FRYHCSODNHYDPU-UHFFFAOYSA-N 0.000 claims 1
RQKYHDHLEMEVDR-UHFFFAOYSA-N oxo-bis(phenylmethoxy)phosphanium Chemical compound C=1C=CC=CC=1CO[P+](=O)OCC1=CC=CC=C1 RQKYHDHLEMEVDR-UHFFFAOYSA-N 0.000 claims 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims 1
238000000034 method Methods 0.000 abstract description 27
YMDXZJFXQJVXBF-STHAYSLISA-N fosfomycin Chemical compound C[C@@H]1O[C@@H]1P(O)(O)=O YMDXZJFXQJVXBF-STHAYSLISA-N 0.000 abstract description 25
229960000308 fosfomycin Drugs 0.000 abstract description 19
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 abstract description 17
239000004310 lactic acid Substances 0.000 abstract description 8
235000014655 lactic acid Nutrition 0.000 abstract description 8
239000000010 aprotic solvent Substances 0.000 abstract description 6
GYDBYATURBDGIF-UHFFFAOYSA-N (2-methyloxiran-2-yl)phosphonic acid Chemical compound OP(=O)(O)C1(C)CO1 GYDBYATURBDGIF-UHFFFAOYSA-N 0.000 abstract description 5
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 abstract description 4
230000015572 biosynthetic process Effects 0.000 abstract description 4
238000003786 synthesis reaction Methods 0.000 abstract description 4
239000003242 anti bacterial agent Substances 0.000 abstract 1
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 abstract 1
229910010277 boron hydride Inorganic materials 0.000 abstract 1
239000000463 material Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 49
239000000243 solution Substances 0.000 description 35
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
238000005160 1H NMR spectroscopy Methods 0.000 description 22
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 19
239000000203 mixture Substances 0.000 description 18
239000012299 nitrogen atmosphere Substances 0.000 description 17
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 10
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
239000012279 sodium borohydride Substances 0.000 description 10
229910000033 sodium borohydride Inorganic materials 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000007858 starting material Substances 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
238000009835 boiling Methods 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
239000000047 product Substances 0.000 description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
238000004821 distillation Methods 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000006735 epoxidation reaction Methods 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
229940098779 methanesulfonic acid Drugs 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
ALHZEIINTQJLOT-VKHMYHEASA-N [(2s)-1-chloro-1-oxopropan-2-yl] acetate Chemical compound ClC(=O)[C@H](C)OC(C)=O ALHZEIINTQJLOT-VKHMYHEASA-N 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
WTLNOANVTIKPEE-VKHMYHEASA-N (2s)-2-acetyloxypropanoic acid Chemical compound OC(=O)[C@H](C)OC(C)=O WTLNOANVTIKPEE-VKHMYHEASA-N 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
150000001263 acyl chlorides Chemical class 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 3
239000012043 crude product Substances 0.000 description 3
RRJHOMPUEYYASJ-UHFFFAOYSA-N ditert-butyl hydrogen phosphite Chemical compound CC(C)(C)OP(O)OC(C)(C)C RRJHOMPUEYYASJ-UHFFFAOYSA-N 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
125000001624 naphthyl group Chemical group 0.000 description 3
238000010992 reflux Methods 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UCSSIRCJFJPJQQ-LURJTMIESA-N [(2s)-1-methoxy-1-oxopropan-2-yl] 2,2-dimethylpropanoate Chemical compound COC(=O)[C@H](C)OC(=O)C(C)(C)C UCSSIRCJFJPJQQ-LURJTMIESA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000012973 diazabicyclooctane Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical class C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
230000007017 scission Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
150000003460 sulfonic acids Chemical class 0.000 description 2
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
YJBNIUHWKMJZJZ-UHFFFAOYSA-N trihydroxy-methyl-(trimethylsilylmethyl)-lambda5-phosphane Chemical compound C[Si](C)(C)CP(C)(O)(O)O YJBNIUHWKMJZJZ-UHFFFAOYSA-N 0.000 description 2
WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 2
238000010626 work up procedure Methods 0.000 description 2
KRGIHOOBHQHYPM-UHFFFAOYSA-N (1-dimethoxyphosphoryloxy-1-hydroxypropan-2-yl) acetate Chemical compound COP(=O)(OC)OC(O)C(C)OC(C)=O KRGIHOOBHQHYPM-UHFFFAOYSA-N 0.000 description 1
HLKDZBZLLWXTSP-UHFFFAOYSA-N (2-acetyloxy-1-hydroxypropyl)phosphonic acid Chemical compound CC(=O)OC(C)C(O)P(O)(O)=O HLKDZBZLLWXTSP-UHFFFAOYSA-N 0.000 description 1
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
JYOQNYLFMVKQHO-UHFFFAOYSA-N 1,1-bis(trimethylsilyl)urea Chemical compound C[Si](C)(C)N(C(N)=O)[Si](C)(C)C JYOQNYLFMVKQHO-UHFFFAOYSA-N 0.000 description 1
MXMXXUIOCREOTJ-UHFFFAOYSA-N 1,2-dihydroxypropylphosphonic acid Chemical class CC(O)C(O)P(O)(O)=O MXMXXUIOCREOTJ-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
JMRIGIQEMZBLAU-UHFFFAOYSA-N 3,3-dihydroxypropylphosphonic acid Chemical class OC(O)CCP(O)(O)=O JMRIGIQEMZBLAU-UHFFFAOYSA-N 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-UHFFFAOYSA-N 0.000 description 1
125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
DJJDKQCLCAMIKX-UHFFFAOYSA-N CCC(=O)OP(O)=O Chemical compound CCC(=O)OP(O)=O DJJDKQCLCAMIKX-UHFFFAOYSA-N 0.000 description 1
241001227713 Chiron Species 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
239000012448 Lithium borohydride Substances 0.000 description 1
JOOMLFKONHCLCJ-UHFFFAOYSA-N N-(trimethylsilyl)diethylamine Chemical compound CCN(CC)[Si](C)(C)C JOOMLFKONHCLCJ-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
241000862969 Stella Species 0.000 description 1
241000187747 Streptomyces Species 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
KTPLZZFNSCRCDM-UHFFFAOYSA-N [2-(2,2-dimethylpropanoyloxy)-1-hydroxypropyl]phosphonic acid Chemical compound OP(=O)(O)C(O)C(C)OC(=O)C(C)(C)C KTPLZZFNSCRCDM-UHFFFAOYSA-N 0.000 description 1
KOOADCGQJDGAGA-UHFFFAOYSA-N [amino(dimethyl)silyl]methane Chemical class C[Si](C)(C)N KOOADCGQJDGAGA-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical group 0.000 description 1
229910001860 alkaline earth metal hydroxide Chemical group 0.000 description 1
125000003302 alkenyloxy group Chemical group 0.000 description 1
125000005133 alkynyloxy group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
244000052616 bacterial pathogen Species 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
150000001642 boronic acid derivatives Chemical class 0.000 description 1
UCKORWKZRPKRQE-UHFFFAOYSA-N bromo(triethyl)silane Chemical compound CC[Si](Br)(CC)CC UCKORWKZRPKRQE-UHFFFAOYSA-N 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000004649 carbonic acid derivatives Chemical group 0.000 description 1
AOGYCOYQMAVAFD-UHFFFAOYSA-M carbonochloridate Chemical compound [O-]C(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-M 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000004020 conductor Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000003983 crown ethers Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
229940042400 direct acting antivirals phosphonic acid derivative Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
150000003944 halohydrins Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003903 lactic acid esters Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
PGQFEEGXXRXUTC-UHFFFAOYSA-N propanoylphosphonic acid Chemical group CCC(=O)P(O)(O)=O PGQFEEGXXRXUTC-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
235000015067 sauces Nutrition 0.000 description 1
239000003579 shift reagent Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
125000004436 sodium atom Chemical group 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
238000003797 solvolysis reaction Methods 0.000 description 1
241000894007 species Species 0.000 description 1
238000003756 stirring Methods 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
230000009466 transformation Effects 0.000 description 1
VMZOBROUFBEGAR-UHFFFAOYSA-N tris(trimethylsilyl) phosphite Chemical compound C[Si](C)(C)OP(O[Si](C)(C)C)O[Si](C)(C)C VMZOBROUFBEGAR-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)

JP63177950A 1987-07-15 1988-07-15 ホスホン酸誘導体およびそのエナンチオ選択的製造 Pending JPH01104085A (ja)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
IT21303A/87		1987-07-15
IT21303/87A IT1222041B (it)	1987-07-15	1987-07-15	Processo per la preparazione di intermedi per la sintesi della fosfomicina
IT23125/87A IT1223564B (it)	1987-12-21	1987-12-21	Processo per la preparazione di intermedi per la sintesi della fosfomicina
IT23125A/87		1987-12-21

Publications (1)

Publication Number	Publication Date
JPH01104085A true JPH01104085A (ja)	1989-04-21

Family

ID=26327859

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP63177950A Pending JPH01104085A (ja)	1987-07-15	1988-07-15	ホスホン酸誘導体およびそのエナンチオ選択的製造

Country Status (6)

Country	Link
US (1)	US4937367A (el)
EP (1)	EP0299484B1 (el)
JP (1)	JPH01104085A (el)
DE (1)	DE3865384D1 (el)
ES (1)	ES2037770T3 (el)
GR (1)	GR3003256T3 (el)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SG115389A1 (en) *	2000-07-14	2005-10-28	Zeiss Carl Nts Gmbh	Process for electron beam lithography, and electron-optical lithography system
JP2009524606A (ja) *	2006-11-24	2009-07-02	李暁祥	アクラトニウムナパジシル酸塩及びその類似化合物の合成方法
WO2010035664A1 (ja) *	2008-09-24	2010-04-01	田辺三菱製薬株式会社	ビスホスホン酸誘導体の製法
JP2015537050A (ja) *	2012-12-11	2015-12-24	ブラッコ・イメージング・ソシエタ・ペル・アチオニＢｒａｃｃｏＩｍａｇｉｎｇＳ．Ｐ．Ａ．	（ｓ）−２−アセチルオキシプロピオン酸クロリドの連続製造方法

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5731299A (en) *	1992-05-29	1998-03-24	The Procter & Gamble Company	Phosphonosulfonate compounds, pharmaceutical compositions, and methods for treating abnormal calcium and phosphate metabolism
US5470845A (en) *	1992-10-28	1995-11-28	Bristol-Myers Squibb Company	Methods of using α-phosphonosulfonate squalene synthetase inhibitors including the treatment of atherosclerosis and hypercholesterolemia
CN1854146B (zh) *	2005-04-25	2011-06-01	北京科莱博医药开发有限责任公司	由右旋磷霉素制备左旋磷霉素的合成方法
DE112007000280A5 (de) *	2006-02-03	2008-10-30	HÄRING, Thomas	Phosphonsäure-haltige Blends und Phosphonsäure-haltige Polymere
CN117964661B (zh) *	2024-04-01	2024-06-07	深圳创元生物医药科技有限公司	一种磷霉素基因毒杂质c的制备方法

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IE32804B1 (en) *	1968-05-15	1973-12-12	Merck & Co Inc	Preparation of (cis-1,2-epoxypropyl)phosphonic acid and derivatives thereof
US3657282A (en) *	1969-01-23	1972-04-18	Merck & Co Inc	Carboxyepoxyethyl-1-phosphonic acid and derivatives
US3819676A (en) *	1969-04-25	1974-06-25	Merck & Co Inc	Alkyl-or arylsulfonyloxy,alkanoyloxy substituted propylphosphoric acid lower alkyl esters

1988
- 1988-07-12 US US07/217,976 patent/US4937367A/en not_active Expired - Lifetime
- 1988-07-14 DE DE8888111335T patent/DE3865384D1/de not_active Expired - Fee Related
- 1988-07-14 EP EP88111335A patent/EP0299484B1/en not_active Expired
- 1988-07-14 ES ES198888111335T patent/ES2037770T3/es not_active Expired - Lifetime
- 1988-07-15 JP JP63177950A patent/JPH01104085A/ja active Pending
1991
- 1991-12-02 GR GR91401884T patent/GR3003256T3/el unknown

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SG115389A1 (en) *	2000-07-14	2005-10-28	Zeiss Carl Nts Gmbh	Process for electron beam lithography, and electron-optical lithography system
JP2009524606A (ja) *	2006-11-24	2009-07-02	李暁祥	アクラトニウムナパジシル酸塩及びその類似化合物の合成方法
WO2010035664A1 (ja) *	2008-09-24	2010-04-01	田辺三菱製薬株式会社	ビスホスホン酸誘導体の製法
JP2015537050A (ja) *	2012-12-11	2015-12-24	ブラッコ・イメージング・ソシエタ・ペル・アチオニＢｒａｃｃｏＩｍａｇｉｎｇＳ．Ｐ．Ａ．	（ｓ）−２−アセチルオキシプロピオン酸クロリドの連続製造方法
JP2019048818A (ja) *	2012-12-11	2019-03-28	ブラッコ・イメージング・ソシエタ・ペル・アチオニＢｒａｃｃｏＩｍａｇｉｎｇＳ．Ｐ．Ａ．	（ｓ）−２−アセチルオキシプロピオン酸クロリドの連続製造方法

Also Published As

Publication number	Publication date
US4937367A (en)	1990-06-26
EP0299484A1 (en)	1989-01-18
ES2037770T3 (es)	1993-07-01
GR3003256T3 (en)	1993-02-17
DE3865384D1 (de)	1991-11-14
EP0299484B1 (en)	1991-10-09

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